Chesapeake Bay Vacation Rentals

9 Rentals

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Gwynn Virginia Vacation Rentals - Cottage

1BR / 1BA - Sleeps 6 - Gwynn Cottage

Our one bedroom rental is located on a beautiful resort on the Chesapeake Bay. The private bedroom has...

$163 - $240 / nt

Roadside Entrance and Front Yard

3BR / 1.5BA - Sleeps 11 - Sandy Point Home

Located in Westmoreland County at Sandy Point, VA, in the heart of Virginia’s historic Northern Neck,...

$100 - $175 / nt

30 Reviews
Dock area

4BR / 2BA - Sleeps 10 - Reedville Home

We are located at 97 Lucys Lane Reedville Va. 22539 We start with the dock and fun stuff. We can e-...

$225 - $250 / nt

13 Reviews
Sandy Point Virginia Vacation Rentals - Home

4BR / 2BA - Sleeps 13 - Sandy Point Home

Location: Sandy Point, Virginia, USA (2 Hours from Washington D. C., 1. 5 Hours from Richmond, Va)...

$100 - $200 / nt

48 Reviews
Reedville Virginia Vacation Rentals - Home

5BR / 3BA - Sleeps 14 - Reedville Home

Our 110 acre sanctuary is a peninsula with the Chesapeake Bay to our east and private lakes to our north...

$400 - $800 / nt

Colonial Beach Virginia Vacation Rentals - Home

3BR / 3BA - Sleeps 8 - Colonial Beach Home

Main house has two bedrooms and two baths, full kitchen, laundry, hide- away bed in living room. Guest...

$99 - $129 / nt

3 Reviews
Reedville Virginia Vacation Rentals - Home

3BR / 2BA - Sleeps 8 - Reedville Home

Treat yourself to the best view on the Bay! Sparkling water, beach, barrier islands, and a gorgeous...

$300 - $500 / nt

Areas Within the Chesapeake Bay, VA, Region

For families seeking accommodations in vacation rentals, Chesapeake Bay offers many possibilities.
Cape Charles is a quaint seaside village located on Virginia's Eastern Shore, which is connected to the mainland by the Chesapeake Bay Bridge-Tunnel. Cape Charles Beach is quiet, clean, and the ideal spot for families.
Irvington is located on the Northern Neck of Virginia and is home to the Irvington Farmers Market on the first Saturday of the month from May until November. On these dates, more than 100 vendors gather to display homemade crafts, baked goods, cheeses, meats, seafood, clothing, furniture, jewelry, and more.
Onancock is a small waterfront town located on the eastern shore of Virginia. Families lodging in a Chesapeake Bay vacation rental during the months of May through September can book a cruise on the Tangier Island Ferry.
Mathews is a historic maritime community located on the eastern tip of Virginia's Middle Peninsula. With plenty of colonial and Civil War sites to visit, history buffs would have a great time exploring this area.

Sightseeing in Chesapeake Bay & Things to Do

The Chesapeake Bay region of Virginia is an ideal spot for nature lovers: There are many available outdoor activities that are fun for the whole family. The Rappahannock River Valley wildlife refuge offers a variety of outdoor activities, including hunting, fishing, and birdwatching. In addition to these activities, kids can take part in environmental education programs. Some of the most popular tourist activities include boating, paddling, or kayaking along the John Smith National Historic Trail. No boat of your own? No problem. Families lodging in Chesapeake Bay rentals can rent paddle-craft at various park sites along the trail.
The Chesapeake Bay area of Virginia boasts a selection of museums that put the visitor in the shoes of a mariner or fisherman. The Deltaville Museum, Mariners' Museum, Reedville Fisherman's Museum, the Steamboat Era Museum, and the Watermen's Museum are just a few of the sites that preserve the heritage and local history of the area.

Regional Foods & Dining in Chesapeake Bay

With approximately 350 species of fish living in its waters, the bay is famous for its seafood production. Blue crabs, oysters, clams, and rockfish are the bay's most popular regional foods.
With time and patience, families staying in Chesapeake Bay vacation rentals can even catch their own meal and prepare it in the comfort of home. Guests interested in this activity should check the state of Virginia's recreational fishing regulations for further information and license requirements.

When to Visit Chesapeake Bay

The Chesapeake Bay area of Virginia has a humid, subtropical climate: Visitors traveling during peak season should expect temperatures ranging between 70 and 90 degrees. Since Chesapeake Bay is known for its water-related recreation, peak season is during the summer, typically in the months of June and July. Visitors are not limited to these months, however, as many decide to travel in late spring and early autumn. Families seeking accommodations in Chesapeake Bay rentals should book ahead if traveling during peak season because they fill up fast. Browse our listing of homes listed by owner, book online, and save!
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